Document Detail

Formation of a fairly stable diazoate intermediate of 5-methyl-2'-deoxycytidine by HNO2 and NO, and its implication to a novel mutation mechanism in CpG site.
MedLine Citation:
PMID:  11836116     Owner:  NLM     Status:  MEDLINE    
The intermediate produced from 5-methyl-2'-deoxycytidine ((5me)dCyd) by HNO2 and NO treatments was isolated and characterized. When 10mM (5me)dCyd was incubated with 100mM NaNO2 at pH 3.7 and 37 degrees C, a previously unidentified product was formed. The product was identified as a diazoate derivative of (5me)dCyd, 1-(beta-D-2'-deoxyribofuranosyl)-5-methyl-2-oxopyrimidine-4-diazoate ((5me)dCyd-diazoate), on the bases of several measurements including LC/MS. The time course of the concentration change of the diazoate showed a characteristic profile of a reaction intermediate, and the steady state concentration was 2.3 microM (0.023% yield). When an aqueous solution of 10mM (5me)dCyd (10 mL) was bubbled by NO at 37 degrees C under aerobic conditions holding the pH around 7.4, the diazoate was also generated. The yield of the diazoate was 0.041 micromol (0.041% yield) at 20 mmol of NO absorption. At physiological pH and temperature (pH 7.4, 37 degrees C), the diazoate was converted to dThd exclusively with a first order rate constant k=9.1x10(-6) x s(-1) (t(1/2)=21 h). These results show that the diazoate is generated as a relatively stable intermediate in the reactions of (5me)dCyd with HNO2 and NO and further suggest that the diazoate can be formed in cellular DNA with biologically relevant doses of HNO2 and NO.
Toshinori Suzuki; Masaki Yamada; Takanori Nakamura; Hiroshi Ide; Kenji Kanaori; Kunihiko Tajima; Takashi Morii; Keisuke Makino
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  Bioorganic & medicinal chemistry     Volume:  10     ISSN:  0968-0896     ISO Abbreviation:  Bioorg. Med. Chem.     Publication Date:  2002 Apr 
Date Detail:
Created Date:  2002-02-11     Completed Date:  2002-09-11     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9413298     Medline TA:  Bioorg Med Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  1063-7     Citation Subset:  IM    
Institute of Advanced Energy, Kyoto University, Gokasho, 611-0011, Uji, Japan.
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MeSH Terms
Azo Compounds / chemistry,  metabolism*
DNA / drug effects,  genetics,  metabolism
Deoxycytidine / analogs & derivatives*,  chemistry,  genetics,  metabolism*
Deoxycytosine Nucleotides / chemistry,  genetics,  metabolism
Deoxyguanosine / analogs & derivatives*,  chemistry,  genetics,  metabolism
Dinucleoside Phosphates / metabolism
Drug Stability
Models, Genetic
Molecular Structure
Nitric Oxide / metabolism*
Nitrous Acid / metabolism*
Reg. No./Substance:
0/Azo Compounds; 0/Deoxycytosine Nucleotides; 0/Dinucleoside Phosphates; 10102-43-9/Nitric Oxide; 15178-66-2/deoxycytidylyl-(3'-5')-deoxyguanosine; 2382-65-2/cytidylyl-3'-5'-guanosine; 7782-77-6/Nitrous Acid; 838-07-3/5-methyldeoxycytidine; 9007-49-2/DNA; 951-77-9/Deoxycytidine; 961-07-9/Deoxyguanosine

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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